DE69314779D1 - PROCESS FOR PRODUCING BETA-PHENYLISOSERINE AND ANALOG COMPOUNDS - Google Patents

PROCESS FOR PRODUCING BETA-PHENYLISOSERINE AND ANALOG COMPOUNDS

Info

Publication number
DE69314779D1
DE69314779D1 DE69314779T DE69314779T DE69314779D1 DE 69314779 D1 DE69314779 D1 DE 69314779D1 DE 69314779 T DE69314779 T DE 69314779T DE 69314779 T DE69314779 T DE 69314779T DE 69314779 D1 DE69314779 D1 DE 69314779D1
Authority
DE
Germany
Prior art keywords
pct
phenylisoserine
general formula
analog compounds
date sep
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
DE69314779T
Other languages
German (de)
Other versions
DE69314779T2 (en
Inventor
Jean-Dominique Bourzat
Alain Commercon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aventis Pharma SA
Original Assignee
Rhone Poulenc Rorer SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhone Poulenc Rorer SA filed Critical Rhone Poulenc Rorer SA
Publication of DE69314779D1 publication Critical patent/DE69314779D1/en
Application granted granted Critical
Publication of DE69314779T2 publication Critical patent/DE69314779T2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Steroid Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

PCT No. PCT/FR93/00224 Sec. 371 Date Sep. 26, 1994 Sec. 102(e) Date Sep. 26, 1994 PCT Filed Mar. 8, 1993 PCT Pub. No. WO93/17997 PCT Pub. Date Sep. 16, 1993This invention relates to a method for preparing beta -phenylisoserine and analogues thereof having general formula (I) <IMAGE> (I) from an aromatic aldehyde and an alpha -methylarylamine-S, and through a lactam of general formula (II) as described herein. The acids of general formula (I) (R=H) may be used to prepare taxane derivatives having remarkable antitumoral and antileukaemic activity.
DE69314779T 1992-03-10 1993-03-08 PROCESS FOR PRODUCING BETA-PHENYLISOSERINE AND ANALOG COMPOUNDS Expired - Lifetime DE69314779T2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9202821A FR2688499B1 (en) 1992-03-10 1992-03-10 PROCESS FOR THE PREPARATION OF BETA-PHENYLISOSERINE AND ITS ANALOGS.
PCT/FR1993/000224 WO1993017997A1 (en) 1992-03-10 1993-03-08 METHOD FOR PREPARING β-PHENYLISOSERINE AND ANALOGUES THEREOF

Publications (2)

Publication Number Publication Date
DE69314779D1 true DE69314779D1 (en) 1997-11-27
DE69314779T2 DE69314779T2 (en) 1998-02-26

Family

ID=9427518

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69314779T Expired - Lifetime DE69314779T2 (en) 1992-03-10 1993-03-08 PROCESS FOR PRODUCING BETA-PHENYLISOSERINE AND ANALOG COMPOUNDS

Country Status (25)

Country Link
US (2) US5608102A (en)
EP (1) EP0630365B1 (en)
JP (1) JP3278768B2 (en)
KR (1) KR100272650B1 (en)
AT (1) ATE159512T1 (en)
AU (1) AU667886B2 (en)
CA (1) CA2130333C (en)
CZ (1) CZ283613B6 (en)
DE (1) DE69314779T2 (en)
DK (1) DK0630365T3 (en)
ES (1) ES2109509T3 (en)
FI (1) FI113640B (en)
FR (1) FR2688499B1 (en)
GE (1) GEP19981430B (en)
GR (1) GR3025117T3 (en)
HU (1) HU213621B (en)
MX (1) MX9301268A (en)
NO (1) NO304515B1 (en)
NZ (1) NZ249899A (en)
PL (1) PL171551B1 (en)
RU (1) RU2103258C1 (en)
SK (1) SK281297B6 (en)
TW (1) TW252971B (en)
WO (1) WO1993017997A1 (en)
ZA (1) ZA931677B (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2195844C (en) * 1994-07-26 2001-10-09 Ezio Bombardelli Semi-synthetic taxanes with anti-tumoural activity
US6765015B2 (en) * 1995-12-13 2004-07-20 Xechem International, Inc. Halogenated paclitaxel derivatives
WO1999008986A1 (en) * 1997-08-21 1999-02-25 Florida State University Method for the synthesis of taxanes
EP1105118A4 (en) * 1997-11-19 2003-02-26 Xechem Inc Halogenated paclitaxel derivatives
ITMI991483A1 (en) * 1999-07-06 2001-01-06 Indena Spa TAXANIC DERIVATIVES AND PROCEDURES FOR THEIR PREPARATION
WO2001024763A2 (en) 1999-10-01 2001-04-12 Immunogen, Inc. Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
JP2002080435A (en) * 2000-06-26 2002-03-19 Kanegafuchi Chem Ind Co Ltd Method for producing 3-amino-2-hydroxypropionic acid derivative
JP4142444B2 (en) * 2001-03-07 2008-09-03 第一三共株式会社 Method for producing 2-azetidinone derivative
PT1961735E (en) * 2007-02-22 2009-12-21 Indena Spa Process for the preparation of (2r,3s)-3-phenylisoserine methyl ester acetate salt
DK2080764T3 (en) 2008-01-18 2012-09-24 Indena Spa Solid forms of orthataxel
CN102408356A (en) * 2011-09-28 2012-04-11 北京东方协和医药生物技术有限公司 Preparation method of docetaxel chiral side-chain intermediate
SG11201606351VA (en) * 2014-02-03 2016-09-29 Quadriga Biosciences Inc Beta-substituted beta-amino acids and analogs as chemotherapeutic agents
CN111100026A (en) * 2019-12-30 2020-05-05 重庆市碚圣医药科技股份有限公司 Preparation method of taxol oxazole ring side chain intermediate
CN112574134A (en) * 2020-12-30 2021-03-30 重庆市碚圣医药科技股份有限公司 Synthesis method of docetaxel side chain

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2629819B1 (en) * 1988-04-06 1990-11-16 Rhone Poulenc Sante PROCESS FOR THE PREPARATION OF BACCATIN III AND DESACETYL-10 BACCATIN III DERIVATIVES
IT1231751B (en) * 1989-04-12 1991-12-21 Sigma Tau Ind Farmaceuti PROCEDURE FOR THE PRODUCTION OF R (+) AMMINOCARNITINE AND S (-) AMMINOCARNITINE
US5175315A (en) * 1989-05-31 1992-12-29 Florida State University Method for preparation of taxol using β-lactam
US5304670A (en) * 1989-08-23 1994-04-19 Centre National De La Recherche Scientifique Process for the enantioselective preparation of phenylisoserine derivatives
FR2658510B1 (en) * 1990-02-21 1992-04-30 Rhone Poulenc Sante NEW DERIVATIVE OF BETA-PHENYLISOSERINE, ITS PREPARATION AND ITS USE.
US5294737A (en) * 1992-02-27 1994-03-15 The Research Foundation State University Of New York Process for the production of chiral hydroxy-β-lactams and hydroxyamino acids derived therefrom

Also Published As

Publication number Publication date
NO943280D0 (en) 1994-09-05
NO943280L (en) 1994-09-05
RU2103258C1 (en) 1998-01-27
ATE159512T1 (en) 1997-11-15
AU667886B2 (en) 1996-04-18
KR100272650B1 (en) 2000-11-15
GEP19981430B (en) 1998-10-30
MX9301268A (en) 1993-09-01
AU3755793A (en) 1993-10-05
ZA931677B (en) 1993-10-06
US5763628A (en) 1998-06-09
SK108594A3 (en) 1995-02-08
CZ218594A3 (en) 1995-11-15
ES2109509T3 (en) 1998-01-16
WO1993017997A1 (en) 1993-09-16
FR2688499B1 (en) 1994-05-06
TW252971B (en) 1995-08-01
NO304515B1 (en) 1999-01-04
GR3025117T3 (en) 1998-01-30
JPH07504425A (en) 1995-05-18
EP0630365B1 (en) 1997-10-22
CZ283613B6 (en) 1998-05-13
NZ249899A (en) 1996-01-26
RU94045799A (en) 1996-07-20
KR950700234A (en) 1995-01-16
HUT68540A (en) 1995-06-28
SK281297B6 (en) 2001-02-12
CA2130333C (en) 2002-11-26
FI113640B (en) 2004-05-31
EP0630365A1 (en) 1994-12-28
FI944169A (en) 1994-09-09
FR2688499A1 (en) 1993-09-17
DE69314779T2 (en) 1998-02-26
FI944169A0 (en) 1994-09-09
US5608102A (en) 1997-03-04
CA2130333A1 (en) 1993-09-16
HU9402590D0 (en) 1994-11-28
HU213621B (en) 1997-08-28
DK0630365T3 (en) 1998-03-02
PL171551B1 (en) 1997-05-30
JP3278768B2 (en) 2002-04-30

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Legal Events

Date Code Title Description
8364 No opposition during term of opposition
8327 Change in the person/name/address of the patent owner

Owner name: AVENTIS PHARMA S.A., ANTONY, FR

8328 Change in the person/name/address of the agent

Representative=s name: PFENNING MEINIG & PARTNER GBR, 80339 MUENCHEN

8328 Change in the person/name/address of the agent

Representative=s name: MAIWALD PATENTANWALTSGESELLSCHAFT MBH, 80335 MUENC